- Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation
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An efficient, one-pot method for the synthesis of dibenzodiazepinone derivatives involving copper-catalyzed tandem C-N bond formation is reported. The use of various halo amide and 2-iodoaniline derivatives permitted the synthesis of an array of dibenzodiazepinone derivatives in moderate to good yields. Moreover, a dibenzodiazepinone derivative {2-(11-oxo-5H-dibenzo[b,e][1, 4]diazepin-10(11H)-yl)benzonitrile} was utilized to synthesize the triazapentacyclic ring derivative {12-chloro- 8,15,22-triazapentacyclo[13.7.0. 02,7.09,14.016,21]docosa-1(22),2,4,6,9(14),10, 12,16(21),17,19-decaene}.
- Gawande, Sachin D.,Kavala, Veerababurao,Zanwar, Manoj R.,Kuo, Chun-Wei,Huang, Wen-Chang,Kuo, Ting-Shen,Huang, Hsiu-Ni,He, Chiu-Hui,Yao, Ching-Fa
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p. 2599 - 2608
(2014/09/17)
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- Structure-activity relationship-guided development of retinoic acid receptor-related orphan receptor gamma (RORγ)-selective inverse agonists with a phenanthridin-6(5H)-one skeleton from a liver X receptor ligand
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Retinoic acid receptor-related orphan receptors (RORs), which belong to the nuclear receptor superfamily, regulate many physiological processes, including hepatic gluconeogenesis, lipid metabolism, immune function and circadian rhythm. Since RORs resemble liver X receptors (LXRs) in the fold structure of their ligand-binding domains, we speculated that ROR-mediated transcription might be modulated by LXR ligands, in line with the multi-template hypothesis. Therefore, we screened our LXR ligand library for compounds with ROR ligand activity and identified a novel ROR ligand with a phenanthridin-6(5H)-one skeleton. Structure-activity relationship studies aimed at separating ROR inverse agonistic activity from LXR-agonistic activity enabled us to develop a series of ROR inverse agonists based on the phenanthridin-6(5H)-one skeleton, including a RORγ-selective inverse agonist.
- Nishiyama, Yuko,Nakamura, Masahiko,Misawa, Takashi,Nakagomi, Madoka,Makishima, Makoto,Ishikawa, Minoru,Hashimoto, Yuichi
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p. 2799 - 2808
(2014/05/06)
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- Structural development studies of anti-hepatitis C virus agents with a phenanthridinone skeleton
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A phenanthridinone skeleton was derived from our previous researches on thalidomide and retinoids as a multi-template for generation of anti-viral lead compounds. Structural development studies focusing on anti-hepatitis C virus activity afforded 5-butyl-2-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenanthridin-6(5H)-one (10) and 5-butylbenzo[b]phenanthridin-6(5H)-one (39), which showed EC50 values of approximately 3.7 and 3.2 μM, respectively.
- Nakamura, Masahiko,Aoyama, Atsushi,Salim, Mohammed T.A.,Okamoto, Mika,Baba, Masanori,Miyachi, Hiroyuki,Hashimoto, Yuichi,Aoyama, Hiroshi
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scheme or table
p. 2402 - 2411
(2010/06/20)
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